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[ CAS No. 63503-60-6 ] {[proInfo.proName]}

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Chemical Structure| 63503-60-6
Chemical Structure| 63503-60-6
Structure of 63503-60-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 63503-60-6 ]

CAS No. :63503-60-6 MDL No. :MFCD00161354
Formula : C6H6BClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SDEAGACSNFSZCU-UHFFFAOYSA-N
M.W :156.37 Pubchem ID :2734323
Synonyms :

Calculated chemistry of [ 63503-60-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.28
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 0.02
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : -0.08
Consensus Log Po/w : 0.45

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.24 mg/ml ; 0.00792 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 1.94 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 2.01 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 63503-60-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63503-60-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 63503-60-6 ]
  • Downstream synthetic route of [ 63503-60-6 ]

[ 63503-60-6 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 201230-82-2 ]
  • [ 63503-60-6 ]
  • [ 7094-34-0 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; silver nitrate In acetone at 40℃; for 24 h; Autoclave; Inert atmosphere General procedure: The reaction was carried out in an autoclave containing a 10mL Teflon reaction tube. Pd(PPh3)4 (0.02 mmol), DPPP(0.04 mmol), and a magnetic stir bar were placed in the tubewhich was then capped with a stopper and flushed withargon. Then, aryl boronic acid (1 mmol), AgNO3 (1 mmol),and acetone (3 mL) were added to the tube. The tube was putinto the autoclave. Once sealed, the autoclave was purgedseveral times with CO, pressurized to 1 atm at r.t. and thenheated in an oil bath at 40 °C for 24 h. The autoclave wasthen cooled to r.t. and carefully vented to discharge CO in afume hood. Water (10 mL) was added, and the product wasextracted with CH2Cl2 (3 × 15 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated. Thecrude product was purified by column chromatography onsilica gel using a mixture of EtOAc and PE as eluent to givethe products. The identity and purity of the product wasconfirmed by 1H NMR and 13C NMR spectroscopy and MSor HRMS spectrometry.
Reference: [1] Synlett, 2014, vol. 25, # 8, p. 1097 - 1100
[2] Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2411 - 2414,4
  • 2
  • [ 63503-60-6 ]
  • [ 618-46-2 ]
  • [ 7094-34-0 ]
YieldReaction ConditionsOperation in experiment
27% With palladium diacetate; sodium carbonate In water at 0 - 80℃; for 1.33333 h; 10182] To a solution of 8-9 (45.3 g, 0.29 mol), Pd (OAc)2 (3.2 g, 14.3 mmol) and Na2CO3 (48 g, 0.46 mol) in PEG:H20 (600 mE, v/v=1:1), was added 8-8 (50.7 g, 0.29 mol) portionwise at 00 C. for 20 mm. The mixture was stirred at 80° C. for 1 h, and then extracted with EtOAc (3x500 mE). The combined organic layers were washed with brine (2x300 mE), dried with Na2SO4 and concentrated to give a residue. The residue was purified by silica gel chromatography (PE:EA=100:1 to 20:1) to provide 8-10 as a white solid (20 g, 27percent). ‘H NMR (400 MHz, CD3C1): ö 7.78 (s, 1H), 7.66 (d, J=7.7 Hz, 1H), 7.60 (d, J=8.2 Hz, 1H), 7.49-7.43 (m, 1H).
Reference: [1] Patent: US2015/72982, 2015, A1, . Location in patent: Paragraph 0181; 0182
  • 3
  • [ 201230-82-2 ]
  • [ 63503-60-6 ]
  • [ 78-94-4 ]
  • [ 7094-34-0 ]
  • [ 3506-73-8 ]
Reference: [1] Chemical Communications, 2004, # 13, p. 1520 - 1521
  • 4
  • [ 63503-60-6 ]
  • [ 625-99-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1 h; General procedure: A mixture of the arylboronic acid (0.55mmol), KF (96mg, 1.65mmol) and I2 (127mg, 0.50mmol) in 1,4-dioxane (5mL) was stirred at 80°C for 1h. Then it was filtered through silica gel, eluting with Et2O (10mL) and the solvent was removed by rotary evaporation. When necessary, the product was purified by chromatography on silica gel (petroleum ether/Et2O 98:2).
73% With iodine; potassium carbonate In acetonitrile at 80℃; for 9 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
[2] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1122 - 1123
[3] Synlett, 1998, # 2, p. 141 - 142
[4] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
  • 5
  • [ 63503-60-6 ]
  • [ 107-12-0 ]
  • [ 34841-35-5 ]
YieldReaction ConditionsOperation in experiment
72% With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether; sodium hydrogencarbonate In water at 100℃; for 5 h; Autoclave General procedure: The reaction was carried out in an autoclave containing a 10 mL Teflon reactiontube. NiBr2·diglyme (5 molpercent), 1,10-phen (10 molpercent) and a magnetic stir bar wereplaced in the tube. Then, arylboronic acid (1.0 mmol), NaHCO3 (2.0 equiv), H2O (2.0mmol) and alkyl nitrile (1.0 mL) were added to the tube. After that the autoclave wascapped with a stopper. The autoclave was cool down by liquid nitrogen, then createdvacuum at this temperature and added HCFC-244bb (2.0 mL, 2.6 g) by self-suction.Finally the autoclave was wormed in an oil bath at 100 °C for 5 h. After the reaction,the autoclave was cooled to room temperature and vented the excess HCFC-244bb carefully. Water (30 mL) was added to the mixture, and the mixture was extractedwith dichloromethane (3 x 15 mL). The organic layers were washed with brine, driedover Na2SO4, and evaporated the organic solvent by rotatory evaporator. The crudeproduct was then purified by column chromatography.
Reference: [1] Synlett, 2018, vol. 29, # 5, p. 593 - 596
  • 6
  • [ 63503-60-6 ]
  • [ 124156-21-4 ]
  • [ 1128-76-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6013 - 6022
  • 7
  • [ 108-37-2 ]
  • [ 63503-60-6 ]
YieldReaction ConditionsOperation in experiment
57%
Stage #1: With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran; hexaneInert atmosphere
General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 °C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 °C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 °C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried.
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[2] Organic Letters, 2005, vol. 7, # 21, p. 4757 - 4759
[3] Tetrahedron, 2007, vol. 63, # 35, p. 8529 - 8536
  • 8
  • [ 108-37-2 ]
  • [ 121-43-7 ]
  • [ 63503-60-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3630 - 3633
  • 9
  • [ 13283-31-3 ]
  • [ 36229-42-2 ]
  • [ 63503-60-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1983, vol. 259, # 3, p. 269 - 274
  • 10
  • [ 36229-42-2 ]
  • [ 63503-60-6 ]
Reference: [1] Journal of the American Chemical Society, 1934, vol. 56, p. 937,938, 941
  • 11
  • [ 108-37-2 ]
  • [ 13283-31-3 ]
  • [ 63503-60-6 ]
Reference: [1] Journal of Organometallic Chemistry, 1983, vol. 259, # 3, p. 269 - 274
  • 12
  • [ 625-99-0 ]
  • [ 63503-60-6 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571
  • 13
  • [ 63503-60-6 ]
  • [ 99329-53-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1731 - 1735
  • 14
  • [ 63503-60-6 ]
  • [ 30289-28-2 ]
  • [ 145959-21-3 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1251 - 1258
  • 15
  • [ 63503-60-6 ]
  • [ 623-49-4 ]
  • [ 62123-73-3 ]
Reference: [1] Chemical Communications, 2007, # 27, p. 2855 - 2857
  • 16
  • [ 63503-60-6 ]
  • [ 1000025-07-9 ]
Reference: [1] Patent: US2012/309977, 2012, A1,
[2] Patent: WO2016/153996, 2016, A1,
  • 17
  • [ 63503-60-6 ]
  • [ 939430-30-5 ]
Reference: [1] Journal of Materials Chemistry, 2011, vol. 21, # 47, p. 19058 - 19062
[2] Patent: WO2012/140243, 2012, A1,
[3] Patent: CN103396355, 2016, B,
  • 18
  • [ 63503-60-6 ]
  • [ 1415226-40-2 ]
Reference: [1] Patent: US2012/309977, 2012, A1,
[2] Patent: WO2016/153996, 2016, A1,
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